Jim Gregory was the St. Michael's Majors trainer and General Manager when they captured the Memorial Cup title in 1961. (Imperial Oil-Turofsky/HHOF)

Born November 4, 1935 in Port Colborne, Ontario, Jim Gregory grew up in nearby Dunnville, where he learned a passion for the game that would define his remarkable career. "My interest in hockey started with playing road hockey," he explained. "We lived in a factory-owned community. There were ten houses on our street and in each one of the houses was an employee of the Monarch Knotting Company. After school, we used to play hockey on the road. I started playing hockey in an organized league when I was about 8 or 9."

Like so many Canadians, 'Hockey Night in Canada' played a role in nurturing a love of hockey. "Both my mother and my father were interested in hockey and we used to have the Leaf games on, listening to Foster Hewitt," recalled Gregory. "The Leafs were my favourite team, and Ted Kennedy was my favourite player. There was a good reason for that. I was born in Port Colborne, about 25 miles down the road from Dunnville, and the place where I was born and where he was born was less than a block apart. Of course, he was a key member of the Leafs at the time (when I was growing up). When I came to Toronto, he took a special interest in me and made sure I was looked after. I think that that association, although it really was just a hello at the beginning, certainly didn't hurt me in respect to Conn Smythe." The lilt in Gregory's voice quickly changed complexion. "I was with Ted Kennedy the night he died (August 14, 2009)."

Jim dreamed of a career in the National Hockey League and many in the area believed he may have the tools to move beyond Dunnville in order to pursue his hockey dreams. "

I had a hockey coach who coached our Midget and Juvenile teams in Dunnville. I played a little bit ahead of myself. We had a strong line, very competitive, and being so close to Hamilton, there was a Junior 'A' team there (the Hamilton Tiger Cubs) and my two linemates and me were all given the opportunity to go to the Junior 'B' camp.

Jim Gregory and the Toronto Marlboros celebrating with the Robertson Cup in 1964. (Graphic Artists/HHOF)

But I had three cousins who had gone to St. Michael's College School (a private boys' high school run by the Basilian Fathers) and my mother had always drilled it into me to keep St. Mike's as a goal, so I figured if I had a chance to play hockey in Hamilton, I could play hockey in Toronto, so I chose to go to St. Mike's."

In 1953, Jim moved to Toronto to attend the highly respected St. Michael's College School, and targeted a spot on one the school's Junior hockey teams. "My first tryout was with the Junior 'B's', but I only lasted two practices (before he was cut). I had a gift  I could score, but my skating wasn't up to par with the other fellows." Jim was so upset that he made plans to leave St. Michael's College School. "This was the end of September, so I figured I still had a chance to play hockey in Hamilton. I phoned my linemates, but in the meantime, Father (David) Bauer, who was my homeroom teacher, told me to settle down, that he'd get me another try-out with the (Junior 'B') Buzzers. This time, I lasted three practices! By that time, it was too late to go to Hamilton. Father Bauer saw that I was really upset. I signed up to play Juvenile and became assistant coach of the Midget team that he was coaching."

The school's teams were considered some of the finest competitors in any league in which they competed. While Gregory was disappointed by not being able to further his playing career, he was unknowingly set on a path that would ultimately lead him to the Hockey Hall of Fame. He was able to learn the nuances of hockey from Bob Goldham and Honoured Members Joe Primeau and Father David Bauer, all of whom coached the Junior 'A' St, Michael's Majors. "During that time, Father Bauer took me more under his wing and I tried to take on a lot of the things from him that took away from his coaching, and he really appreciated it. Through that, I got to do a little work with the Toronto Maple Leafs, who sponsored St. Mike's."

Jim Gregory proudly showing off the George Richardson Trophy, the Memorial Cup and the Robertson Cup he captured as General Manager of the Toronto Marlboros. (Graphic Artists/HHOF)

But all was not calm on the hockey front at the school at that time. There was a faction within the administration that believed that hockey was becoming a distraction, and took the school too far away from its core purpose. "The priests were getting tired of the concessions they had to make for hockey players being away (on the road playing games). St. Mike's was trying to establish itself as an academic school, and there were 20 Junior 'A' players and 20 Junior 'B' players in a school of 550 or 600 kids, and if the marks of the hockey players weren't all really good, it brought the overall average down, which didn't help the school's academic standing. In 1959, they started talking about getting out of hockey. They felt it was almost like the hockey program was professional, which, in many ways, it was."

The St. Michael's Majors won the prestigious Memorial Cup as the premier Junior 'A' team in Canada in 1961. "The Basilian Fathers had had enough," admitted Jim. "They made a determination that the players were away too much." In short order, that spring, the Majors played Guelph and two weeks in Edmonton for the Memorial Cup. "That was the end of the hockey program," said Gregory.

But Stafford Smythe, who along with Harold Ballard and John Bassett was the Leafs' owner at the time, didn't want to lose his affiliation with St. Michael's. The relationship had proven incredibly fruitful for the Maple Leafs, providing them with, among many others, Dick Duff, Dave Keon and Frank Mahovlich. "To keep St. Mike's' hockey program going, Stafford created the Toronto Metro Junior Hockey League, with St. Mike's, the Toronto Marlboros, Whitby, Brampton, Unionville and Oshawa," recalled Gregory. The configuration lasted but one year. St. Mike's liked this league much better because there were no road trips, but in spite of the fact that the franchise enjoyed success, going to the Ontario finals against Hamilton that year, in April, the school notified Gregory and the Leafs that they would not be continuing the hockey program after that spring.

Jim Gregory replaced Punch Imlach as the Toronto Maple Leafs' General Manager in April of 1969. (Graphic Artists/HHOF)

Gregory scurried around to find a new home for the team, speaking with Kitchener, among other potential homes, but eventually, Jim and the Leafs' chief scout selected a Toronto school, Neil McNeil. With Gregory as coach and manager, the team and program almost identical to what had been at St. Mike's the previous year, the team won the league championship in 1963, but after one season, the Metro Junior Hockey League folded. "The teams in the league couldn't afford to carry on," explained Gregory. The Oshawa Generals and Toronto Marlboros returned to the Ontario Hockey Association for the 1963-64 season. The Marlboros' roster was comprised of the best of the Marlboros and the Neil McNeil Maroons. The powerhouse went on to win the Memorial Cup that spring. "We had an unbelievable squad," smiled Gregory. The team won another Memorial Cup championship in 1967.

"I was coach and manager of the Marlboros but I was also the director of the amateur farm system," stated Gregory. "The rules were that for every professional team that you were involved with, whether you owned them or not, as long as you had a working agreement with them, you were allowed to have two sponsored teams." At the time, the Leafs had the Rochester Americans in the American Hockey League, the Victoria Maple Leafs in the Western Hockey League and the Tulsa Oilers in the Central Professional Hockey League. So, with four professional teams (including the Toronto Maple Leafs), Toronto had junior sponsorships with Three Rivers, Quebec, the Toronto Marlboros, Calgary, Alberta, Melville, Saskatchewan, Winnipeg, Manitoba and briefly, Sudbury in the EPHL. "Bob Davidson coordinated all those teams," Jim stated. "My job was to get players for these teams and to make the Reserve List as good as it could be. When I got that job, I thought that was going to be my job for life. I had no dreams of going beyond that. There were six teams back then and when a guy got a job in the NHL, he stayed there forever."

Sponsorship ended in the 1960s. "Stafford Smythe was one of the proponents of the Entry Draft. Stafford recognized that the Boston Bruins and New York Rangers were in a position that they might never get out of." The Bruins missed the playoffs each season from 1959-60 to 1966-67 while the Rangers missed the playoffs in six of those eight seasons. "Everyone in our organization was against starting a draft. We knew we could get better players without the draft. Stafford sacrificed the team's supremacy for the good of the league."

Since 1998, Jim Gregory has served as Chairman of the Hockey Hall of Fame's Selection Committee. (Dave Sandford/HHOF)

Already in the employ of the Toronto Maple Leafs' organization, Jim joined the Western Hockey League's Vancouver Canucks as head coach in 1967-68. In 1968-69, he was hired to assist Punch Imlach and Bob Davidson with the Maple Leafs, focusing on scouting duties. "I was down in Oklahoma watching Tulsa, our farm team, in April 1969. The phone rang and the manager of the Oklahoma City Blazers came out and said, 'Jim, there's a phone call for you. It's Stafford Smythe.' Some of the other scouts I was sitting with were laughing, so I figured it was a joke. I said, 'Tell him I'm busy.' Twenty minutes later, Stafford called again. I took this call and he asked why I didn't take his previous call. I told him I thought the scouts were messing around with me. He said, 'I want you to come home.' I said, 'Why? I'm watching this series. There's another game tomorrow.' He said, 'Well, you're the new manager of the Toronto Maple Leafs.' He had fired Imlach that night and he made his decision. I almost blew it!"

At the age of 33, Jim Gregory replaced Imlach as the Leafs' General Manager. "I met with Stafford and the Board of the Leafs. They wanted me to look at the entire organization  the team, the staff and budgets, then report back to them in ten days. I knew the players, as I had been with the Leafs for six or seven years, but I didn't know the budgets. The entire budget for players, coach, the manager and trainer in 1969 was $750,000! I worked for Stafford until his death in 1971. He ran the hockey operations. After he died, (Harold) Ballard took over. Ballard went to jail in 1972 until 1974. During that time, I reported to a committee headed by George Mara (chairman of the Board of Directors). From 1974 to 1979, I worked for Ballard."

Gregory stayed in the role of general manager for ten seasons. "I tried to hire great people, like Johnny McLellan. We started a scouting system, too. I hired Frank Bonello and five full-time scouts." During his tenure, Jim made many highly positive changes to the franchise. He was one of the first NHL managers to recognize Europe as a talent pool for the NHL. Gregory quickly emerged as a strong executive and the Maple Leafs made the playoffs in eight of the ten seasons he ran the Toronto Maple Leafs.

"I lost my job in 1979," shrugged Gregory. "The Leafs got beat out by the Islanders that year in the playoffs. After the series, Ballard saw me in the parking garage and said, 'Perk up.' I said, 'Every day I read in the paper that I'm getting fired.' He said, 'Oh, don't worry about that. You're too valuable around here. You're going to be here forever. Go off and enjoy your vacation.' I went to my cottage and got a call from Brian O'Neill. He said, 'John Ziegler wants to talk to you about a job.' I said 'What kind of a job?' He said, 'You're not working for the Leafs anymore, are you?' That's how I found out I'd been fired! I got dressed and drove right down to the city. I went to my office and Punch Imlach (who had been hired to return as GM of the club) was already there. He said, 'What're you doing here?' I said, 'I want to find out what's going on.' Two days later, I met John Ziegler and he offered me a job with the league. I told him, 'I haven't even been told I've been fired!' It took Ballard five days to finally tell me."

Jim was hired by the National Hockey League as Director of Central Scouting. In 1986, he was named Executive Director of Hockey Operations for the NHL. Today, Gregory continues as Senior Vice President, Hockey Operations and Supervision for the NHL. Under his management, the implementation of video goal reviews was introduced.

In addition to his duties with the NHL, Jim has served as Chairman of the Hockey Hall of Fame's Selection Committee since 1998, with the notable exception of 2007. On hiatus due to illness, Gregory stepped down from his duties with the Hockey Hall of Fame, and the remaining members of the Selection Committee took advantage of his absence to select Jim as an Honoured Member of the Hockey Hall of Fame in the Builder category. Humbled, Gregory beamed. "Being inducted into the Hall of Fame was unbelievable!"

Jim Gregory, whose failed hockey career allowed him to rise through the ranks from assistant coach at his high school to become the general manager of his longtime favourite hockey team, has established his legacy as one of the most successful, innovative and well-liked executives in the history of the National Hockey League.

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Kevin Shea is the Editor of Publications and Online Features for the Hockey Hall of Fame.